Tag: M.W=100-200

Reference of 13674-16-3 , The common heterocyclic compound, 13674-16-3, name is Methyl 2-hydroxy-3-phenylpropanoate, molecular formula is C10H12O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Phenyltrimethylammoniun tribromide (9.45 g, 25.1 mmol) was added under nitrogen in portions over approximately 2 h to a solution of 1-(6-methoxy-naphthalen-2-yl)-ethanone (5.05 g, 25.2 mmol) in 50 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 0.5 h. and then 250 mL of cold water was added. The solid present was collected by filtration, rinsed with 50 mL of water and dried under reduced pressure to give 6.66 g of a tan solid. Recrystallization of the solid from isopropyl alcohol gave 2-bromo-1-(6-methoxy-2-naphthyl)ethanone (4.07 g, 58%) as a brown solid, mp 109-112 C. Elemental Analysis for C13H11BrO2Calc’d: C, 55.94; H, 3.97; N, 0.00. Found: C, 56.03; H, 3.94; N, 0.00. Step 2: 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole. Thiobenzamide (447 mg, 3.26 mmol) was added under nitrogen to a solution of (2-bromo-1-(6-methoxy-2-naphthyl)ethanone (906 mg, 3.25 mmol), prepared in the previous step, in 25 mL of absolute ethanol at approximately 70 C. After the addition the reaction was refluxed for 2 h. The solid was collected by filtration, rinsed with absolute ethanol and dried under reduced pressure to give 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (909 mg, 88%) as a white solid, mp 191-193 C. Elemental Analysis for C20H15NOS Calc’d: C, 75.68; H, 4.76; N, 4.41. Found: C, 75.37; H, 4.65; N, 4.31. Step 3: 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol. A solution of 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (804 mg, 2.53 mmol), prepared in the previous step, in 50 mL of glacial HOAc plus 25 mL of 48% HBr was stirred under nitrogen at 120 C. for 3 h. The solvent was removed under reduced pressure and the residue partitioned between 10% methanol-methylene chloride and 5% NaHCO3. (Note: The solid that did not dissolve in either layer was collected by filtration and saved as the HCL salt of the desired product). The aqueous layer was separated and extracted three times with 10% methanol-methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (650 mg, 85%) as a brown solid, mp 194-197 C. Elemental Analysis for C19H13NOS Calc’d: C, 75.22; H, 4.32; N, 4.62. Found: C, 74.22; H, 4.12; N, 4.43 Step 4: 2-Hydroxy-3-phenyl-propionic acid methyl ester. Hydrogen chloride was bubbled for 15 minutes into a solution of 2-hydroxy-3-phenyl-propionic acid (10.0 g, 60 mmol) in 100 mL of methanol at room temperature. The vessel was sealed and then stirred overnight at room temperature. The reaction was made basic by the addition of 5% NaHCO3 and then concentrated under reduced pressure to remove the methanol. The residue was diluted with water and extracted with ethyl acetate. The organic layer was extracted with saturated NaCl, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 2-hydroxy-3-phenyl-propionic acid methyl ester (9.7 g, 90%) as a yellow oil, MS m/z 180 [M]+. Elemental Analysis for C10H12O3 Calc’d: C, 66.65; H, 6.71; N, 0.00. Found: C, 66.52; H, 6.86; N, 0.29 Step 5: 3-Phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester. Triethylamine (931 muL, 6.68 mmol) was added under nitrogen to a solution of 2-hydroxy-3-phenyl-propionic acid methyl ester (1.00 g, 5.57 mmol), prepared in the previous step, in 20 mL of chloroform (99.9%; free of ethanol) at dry ice-acetone temperature. Trifluoromethanesulfonic anhydride (1.03 mL, 6.13 mmol) was then added dropwise over 15 minutes. The cooling bath was removed and the reaction was stirred overnight at room temperature. The reaction was extracted with 1 N HCl, 5% NaHCO3, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1.53 g a brown oil. Purification of the oil on 100 g of silica gel (230-400 mesh) using 3:1 methylene chloride:hexane as the eluent gave 3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (1.106 g, 64%) as clear oil. Elemental Analysis for C11H11F3O5S Calc’d: C, 42.31; H, 3.55; N, 0.00. Found: C, 42.15; H, 3.35; N, 0.14 Step 6: Methyl 3-phenyl-2-{[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy} propanoate. A mixture of 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (247 mg, 0.814 mmol), prepared in step 3,3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (387 mg, 1.24 mmol), prepared in the previous step, and cesium carbonate (532 mg, 1.63 mmol) in 20 mL of acetone was stirred under nitrogen at room temperature for 17 h. The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 449 mg of a brown oil. Purification of the oil on 300 g of silica gel (230-400 mesh) using 1:1 to 3:2 methylene chloride:hexane as the eluent gave methyl 3-phenyl-2…

The synthetic route of 13674-16-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2006/52420; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29683-23-6, Tetrahydro-2H-thiopyran-4-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of Tetrahydro-2H-thiopyran-4-ol, blongs to alcohols-buliding-blocks compound. Safety of Tetrahydro-2H-thiopyran-4-ol

A mixture of tetrahydrothiopyran-4-ol (98.00 g, 829.10 mmol, 1.00 eq), 2,2,2-trifluoroacetamide (141 .00 g, 1.25 mol, 1.50 eq), Phl(OAc)2 (401 .00 g, 1 .24 mol, 1 .50 eq), MgO (134.00 g, 3.33 mol, 4.01 eq) and Rh2(OAc)4 (1 1 .00 g, 24.89 mmol, 0.03 eq) in DCM (1 .50 L) was stirred at 20 for 18 hrs. TLC (DCM/MeOH = 20/1 , Rf = 0.35) showed source material was consumed completely and three new spots were found. The mixture was filtered through a pad of Celite and the filter cake was washed with DCM (400 mL*2). The combined filtrates were concentrated under vacuum. The residue was purified by silica gel column (DCM/MeOH = 40/1 to 20/1 ) to give the title compound (83.00 g, 270.78 mmol, 32.66% yield, 80% purity) as light yellow solid. LCMS (method 2): Rt = 0.655 min, m/z = 122.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29683-23-6, Tetrahydro-2H-thiopyran-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER HEALTHCARE CHINA; WORTMANN, Lars; SAUTIER, Brice; EIS, Knut; BRIEM, Hans; BOeHNKE, Niels; VON NUSSBAUM, Franz; HILIG, Roman; BADER, Benjamin; SCHROeDER, Jens; PETERSEN, Kirstin; LIENAU, Philip; WENGNER, Antje, Margret; MOOSMAYER, Dieter; WANG, Qiuwen; (278 pag.)WO2019/201848; (2019); A1;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 558-42-9, name is 1-Chloro-2-methyl-2-propanol. This compound has unique chemical properties. The synthetic route is as follows. name: 1-Chloro-2-methyl-2-propanol

[00302j 5-(2-fluoro-2-methyl-propoxy)-6-methoxy-pyridine-2- carboxylic acid [00303j A mixture of 1-chloro-2-methyl-propan-2-ol (10 mL, ), 4- hydroxy-3-methyl-benzoic acid (2.0 g, 13.2 mmol), K2C03 (7.3 g, 52.7 mmol), H20 (6.0 mL) and ethanol (60 mL) was heated at 80 °C overnight. The reaction mixturewas cooled to rt, partitioned between iN NaOH and EtOAc and the layers separated. The organic layer was washed with iN NaOH (2x) and the combined aqueous layers were washed with EtOAc. The combined organics were concentrated under reduced pressure and diluted with EtOH (15 mL). The mixture was treated with H20 (2 mL) and NaOH (1.0 g, 26.3 mmol). The reaction mixture was stirred at 40 °C for 4 h. Thereaction mixture was poured into iN NaOH and extracted with ether (2x). The pH was brought to 2-3 with 6N HC1 and the aqueous material was extracted with EtOAc (3x). The organics were combined, washed with saturated aqueous NaC1, dried (Na2SO4), filtered, and evaporated to dryness. The material was triturated with ether to provide 4-(2-hydroxy-2-methyl-propoxy)-3-methyl-benzoic acid (2.2 g, 75percent) as a white solid.?H NMR (400 MHz, DMSO) d 7.75 (dd, J = 8.5, 2.0 Hz, 1H), 7.73 – 7.70 (m, 1H), 6.96 (d, J = 8.6 Hz, 1H), 4.67 (s, 1H, OH), 3.76 (s, 2H), 2.20 (s, 3H), 1.22 (s, 6H). ESI-MS mlz calc. 224.1, found 225.5 (M+1) Retention time: 1.06 mm (3 mm run).

With the rapid development of chemical substances, we look forward to future research findings about 558-42-9.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DENINNO, Michael, Paul; ANDERSON, Corey; CONROY, Erica, Lynn; FRIEMAN, Bryan, A.; GROOTHENHUIS, Peter, Diederik Jan; HADIDA-RUAH, Sara, Sabina; HURLEY, Dennis, James; PIERRE, Fabrice Jean, Denis; SILINA, Alina; UY, Johnny; ZHOU, Jinglan; WO2015/6280; (2015); A1;,
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Application of 3973-18-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3973-18-0, name is Propynol ethoxylate, molecular formula is C5H8O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[Synthesis 7]Production of 2-((4-methylcyclohexa- l,4-dienyl)methoxy)ethyl4-methylbenzenesulfonate and 2-((5-methylcyclohexa- l,4-dienyl)methoxy)ethyl 4-methylbenzenesulfonate (1,4type) (1,4type)+ +In 400 ml of toluene, 100.00 g (0.59 mol) of the diene alcohols obtained in Synthesis 6, 90.29 g (0.89 mol) of triethylamine, 73.20 g (0.89 mol) of 1-methylimidazole were dissolved. To this solution cooled in an ice bath, a toluene solution (400 ml) of 130.33 g (0.68 mol) of p-toluenesulfonyl chloride was added dropwise slowly, followed by stirring at room temperature for 1 hour. Water was added thereto, and phase separation was conducted. The obtained organic layer was washed with 15% sulfuric acid, water, and saturated aqueous sodium hydrogen carbonate in this order. The solvent was removed by distillation under reduced pressure. Thus, 188.01 g of the target tosylates were obtained as a colorless oily substance. Yield: 98.1% (l,4-type/l,5-type=91/9). ?-NMR (CDC13, 300 MHz) ?:1.67 (s, 3H), 2.44 (s, 3H), 2.58 (brs, 4H), 3.58-3.55 (m, 2H), 3.84 (s, 2H), 4.18-4.14 (m, 2H), 5.41-5.40 (m, 1H), 5.64-5.63 (m, 1H), 7.33 (d, J=8.3 Hz, 1H), 7.80 (d, J=8.3 Hz, 1H);HRMS (ESI):[M+H]+ calcd for C17H22O4S: 323.1312; found: 323.1325

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 3973-18-0, Propynol ethoxylate.

Reference:
Patent; TAKASAGO INTERNATIONAL CORPORATION; TANAKA, Shigeru; TOUGE, Taichiro; NARA, Hideki; ISHIDA, Kenya; WO2013/65867; (2013); A1;,
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Synthetic Route of 41175-50-2 ,Some common heterocyclic compound, 41175-50-2, molecular formula is C12H15NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Compound 26 (0.13 g, 0.69 mmol) was dissolved in 1 mL MeOH. The solution was chilled in an ice bath, then was treated with HC1 (2 M, 10 mL). After 15 mins, />-nitrobenzenediazonium tetrafluoroborate (0.18 g, 0.76 mmol) was added to the solution in 5 portions over 15 mins, then stirred at 0 C for additional 1 h. During which time, the color of the reaction mixture changed from orange to dark red. After which, the solution was carefully basified with solid K2CO3 until pH value of the solution rose above 8. The deep red precipitate was collected via vacuum filtration and washed with small portions of DI water. The product was left in the funnel and air dried overnight to afford compound 36 (186 mg, 80%) as a dark red solid, which was used for the next step without further purification.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 41175-50-2, 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OREGON HEALTH & SCIENCE UNIVERSITY; GIBBS, Summer L.; WANG, Lei G.; BARTH, Connor W.; (159 pag.)WO2020/23911; (2020); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1124-63-6, 3-Cyclohexylpropan-1-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

3-Cyclohexylpropan-1-ol (10 mmol) was refluxed overnight with bromic acid (10 mmol). After adding ice water,The reaction mixture was extracted with ethyl acetate to give 3- (bromopropyl) cyclohexane. The crude mixture was reacted with phthalimide (15 mmol) in THF solution (20 ml) to obtain a white solid phthalimide derivative. This was filtered and then reacted with hydrazine (98%, 63 mmol) in anhydrous ethanol (15 ml) at 60 C for 10 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate to give a 3-cyclohexylpropylamine compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1124-63-6, 3-Cyclohexylpropan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
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Reference of 14426-20-1 ,Some common heterocyclic compound, 14426-20-1, molecular formula is C6H16ClNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Chenodeoxycholic acid (2.0 g, 5.1 mmol), DMAP (0.92 g, 7.6 mmol) and diethylaminoethanol hydrochloride (1.17 g, 7.6 mmol) were mixed and dissolved in dichloromethane (15 mL). ), EDCI (1.46 g, 7.6 mmol) was added in portions. After stirring at room temperature for 3 hours, water and dichloromethane were added and extracted three times. The organic phase was washed twice with saturated ammonium chloride and washed with saturated brine.Dry Na2SO4, concentrate by filtration,After column chromatography, chenodeoxycholic acid 2-(diethylamino)ethyl ester (2.99 g, 80%) was obtained.2-(Diethylamino)ethyl chenodeoxycholate (2.0 g, 4.1 mmol) was dissolved in 10 mL of glacial acetic acid, heated to 50 C for 2 hours, and glacial acetic acid was concentrated to obtain chenodeoxycholic acid 2 -(Diethylamino)ethyl acetate (2.24 g, 100%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 14426-20-1, 2-(Diethylamino)ethanol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ningbo Bai Naxi Pharmaceutical Co., Ltd.; Li Xiaochuan; (20 pag.)CN108218945; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 67622-86-0, 2-Methyl-1-(methylamino)propan-2-ol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Application In Synthesis of 2-Methyl-1-(methylamino)propan-2-ol, blongs to alcohols-buliding-blocks compound. Application In Synthesis of 2-Methyl-1-(methylamino)propan-2-ol

To a suspension of l-methyl-4-nitro-lH-pyrazole-3-carboxylic acid (639 mg, 3.7 mmol) and 2- methyl-l-(methylamino)propan-2-ol (500 mg, 4.85 mmol) in THF (15 mL) were added HATU (1.57 g, 4.12 mmol) and N-methylmorpholine (2.13 mL, 19.4 mmol) at ambient temperature. The mixture was heated to 70 C and stirred for 16 h. After cooling down to ambient temperature, the reaction mixture was poured into 20 mL HC1 (2N aqueous solution) and extracted with ethyl acetate (2 x 100 mL).The organic layers were washed with water, brine and the solvent was evaporated. The aqueous layer was back-extracted with dichloromethane, dried and concentrated in vacuo. Both residues were combined to give 2.75 g of a semi-solid yellow material. The crude material was purified by silica gel chromatography using a methanol/ethyl acetate gradient to yield the product (1.2 g, 90 %) as colorless oil.MS: M = 257.3 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67622-86-0, 2-Methyl-1-(methylamino)propan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); A1;,
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Related Products of 3840-31-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 3840-31-1 as follows.

A solution of alcohol 30?22 (396 mg, 2 mmol), imidazole (300 mg, 4.4mmol), and TBSCl (332 mg, 2.2 mmol) in anhyd CH2Cl2 (4 mL) was stirred at overnight at`1234/7458-+ * r.t. H2O (5 mL) and CH2Cl2 (20 mL) were addedto the mixture, and the organic layer was separated, washed successivelywith sat. aq NaHCO3 (5 mL), H2O (2 × 5 mL), and brine (5 mL),then dried (MgSO4) and filtered. The filtrate was concentrated in vacuoand the residue was purified by flash column chromatography [silicagel, EtOAc-PE (1:25)] to give a colorless oil; yield: 569 mg (91%).IR (KBr): 2962, 2928, 2857, 1596, 1499, 1459, 1378, 1017, 832, 775cm-1.1H NMR (300 MHz, CDCl3): delta = 6.57 (s, 2 H), 4.69 (s, 2 H), 3.85 (s, 6 H),3.83 (s, 3 H), 0.96 (s, 9 H), 0.11 (s, 6 H).13C NMR (75 MHz, CDCl3): delta = 153.16, 137.14, 136.78, 102.80, 64.86,60.78, 55.96, 25.89, 18.36, -5.28.MS (ESI, MeOH): m/z = 335 [M + Na]+.HRMS-ESI: m/z [M + Na]+ calcd for C16H28NaO4Si: 335.1655; found:335.1663.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3840-31-1, its application will become more common.

Reference:
Article; Zhang, Qi; Kang, Xiuqin; Long, Lei; Zhu, Lijuan; Chai, Yonghai; Synthesis; vol. 47; 1; (2015); p. 55 – 64;,
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Electric Literature of 71176-54-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 71176-54-0, name is (5-Amino-1,3-phenylene)dimethanol, molecular formula is C8H11NO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Compound 27:25 26 27[227] To a solution of 5-nitro-m-xylene-alpha,alpha’-diol 25 (1.07 g, 5.84 mmol) in methanol (50 mL) was added Pd/C (10percent, 311 mg, 0.29 mmol). Hydrogen was introduced to replace the air then the mixture was hydrogenated (H2, 5 psi) for 2 hours at room temperature. The solution was filtered through celite and the filtrate was evaporated by rotary evaporation in vacuo to give compound 26 as a white solid (900 mg, y = 100percent). 1H NMR (400 MHz, MeOD): delta 6.71 (s, IH), 6.66 (s, 2H), 4.51 (s, 4H); 13C NMR (400 MHz, MeOD): delta 148.9, 143.8, 116.7, 114.3, 65.5; It was dissolved in anhydrous acetonitrile (30 mL) and ethyl bromoacetate (443 mul, 4.67 mmol) and potassium carbonate (807 mg, 5.84 mmol) were added. The mixture was put in a 86 0C oil bath and refluxed for 17 hours. The reaction mixture was removed from the oil bath, cooled to room temperature and diluted with dichloromethane. It was filtered through celite and the solid was washed with dichloromethane. White precipitate appeared in the filtrate. It was col]ected by filtration to give compound 27 (414 mg, y = 39percent) as a white solid. 1H NMR (400 MHz, MeOD): delta 6.67 (s, IH), 6.53 (s, 2H), 4.51 (s, 4H), 3.94 (s, 2H), 3.73 (s, 3H); 13C NMR (400 MHz, MeOD): delta 174.0, 149.7, 143.9, 116.2, 111.6, 65.6, 52.6, 46.5; MS (m/z): found 248.0 (M + Na)+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 71176-54-0, (5-Amino-1,3-phenylene)dimethanol.

Reference:
Patent; IMMUNOGEN, INC.; LI, Wei; FISHKIN, Nathan, Elliott; ZHAO, Robert, Yongxin; MILLER, Michael, Louis; CHARI, Ravi, V., J.; WO2010/91150; (2010); A1;,
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